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Polysiloxane copolymers with terminal hydrophilic polymer chains

a technology of polysiloxane and polymer chain, which is applied in the direction of instruments, optical elements, optics, etc., can solve the problems of corneal swelling, inability to easily circumvent oxygen, and undesirable growth of blood vessels in the cornea

Active Publication Date: 2011-11-01
ALCON INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The solution provides a cost-effective method to create silicone hydrogel contact lenses with hydrophilic surfaces that are non-adherent and maintain high oxygen and ion permeability, addressing the adhesion issues and compatibility challenges of existing methods.

Problems solved by technology

“Soft” contact lenses conform closely to the shape of the eye, so oxygen cannot easily circumvent the lens.
If sufficient oxygen does not reach the cornea, corneal swelling occurs.
Extended periods of oxygen deprivation cause the undesirable growth of blood vessels in the cornea.
However, a silicone hydrogel material typically has a surface or at least some areas of its surface which is hydrophobic (non-wettable).
However, the wetting agents are hydrophilic in nature and have very poor miscibility with some polymerizable hydrophobic components in silicone hydrogel lens formulation.
Choice for such compatibilizing agents is limited.
Without compatibilizing agent, poor miscibility of a wetting agent with a silicone hydrogel lens formulation can cause the turbidity of the lens formulation and adversely affect the optical properties of resultant silicone hydrogel contact lenses.

Method used

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  • Polysiloxane copolymers with terminal hydrophilic polymer chains
  • Polysiloxane copolymers with terminal hydrophilic polymer chains
  • Polysiloxane copolymers with terminal hydrophilic polymer chains

Examples

Experimental program
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Effect test

example 1

Surface Hydrophilicity (Wettability) Tests

[0167]Water contact angle on a contact lens is a general measure of the surface hydrophilicity (or wettability) of the contact lens. In particular, a low water contact angle corresponds to more hydrophilic surface. Average contact angles (advancing) of contact lenses are measured using sessile drop method.

[0168]Oxygen permeability measurements. The oxygen permeability of a lens and oxygen transmissibility of a lens material is determined according to a technique similar to the one described in U.S. Pat. No. 5,760,100 and in an article by Winterton et al., (The Cornea: Transactions of the World Congress on the Cornea 111, H. D. Cavanagh Ed., Raven Press: New York 1988, pp 273-280), both of which are herein incorporated by reference in their entireties. Oxygen fluxes (J) are measured at 34° C. in a wet cell (i.e., gas streams are maintained at about 100% relative humidity) using a Dk1000 instrument (available from Applied Design and Developmen...

example 2

Reaction of Epoxy Terminated PDMS with 2-Hydroxy-2-methyl-1-phenyl-propanone

[0177]2-Hydroxy-2-methyl-1-phenyl-propanone (Daracure 1173, from CIBA) (19.8791 grams) is mixed with 20.0231 grams of epoxy terminated polydimethylsiloxane (PDMS) (DMS-E09 from Gelest), 40 mL of methylene chloride and 0.1530 grams of borontrifluoride tetrahydrofuran complex. The temperature of the reaction mixture is increased from about 22° C. to about 33° C. after the reaction components are mixed. After about 30 minutes the temperature of the reaction mixture is decreased to about 27° C. After about 6 hours at room temperature about 10 mL of methanol is added into the reaction mixture and stirred continuously for several more minutes. The reaction mixture is diluted with about 100 mL of methylene chloride and extracted with 10% sodium carbonate solution (3×50 mL), extracted with water 2×50 mL and then dried over MgSO4. The PDMS-macroinitiator is separated from MgSO4 and methylene chloride is removed by a ...

example 3

Reaction of PDMS Macro-Initiator with DMA: Preparation of Poly(DMA)-PDMS-Poly(DMA)

[0178]About 5.02 grams of the PDMS-macroinitiator from Example 2 is combined with about 30.06 grams of N,N-dimethylacrylamide (DMA) and 100 mL of ethyl acetate in a plastic beaker. A stir bar is added to the mixture and the beaker is sealed with a polyethylene bag. The mixture is stirred while being irradiated with UVA light at an intensity of about 3.5 mW / cm2. After being irradiated for a total of about 6 hours, the reaction mixture is inhibited with about 13 mg of 4-hydroxy-TEMPO dissolved in about 5 mL of ethyl acetate. The mass of the reaction mixture is adjusted to about 160 grams through the addition of ethyl acetate.

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Abstract

The invention provides an actinically-crosslinkable linear polysiloxane copolymer. The actinically-crosslinkable polysiloxane copolymer can be used to prepare a silicone hydrogel contact lens having a hydrophilic surface without post-curing surface treatment. The invention is also related to a silicone hydrogel contact lens obtained from a lens-forming material including an actinically-crosslinkable polysiloxane copolymer of the invention and to a method for making an actinically-crosslinkable polysiloxane copolymer of the invention. In addition, the invention provides a non-crosslinkable linear polysiloxane copolymer capable of being used as a internal wetting agent which can render the surface of a silicone hydrogel contact lens hydrophilic.

Description

[0001]This application claims the benefit under 35 U.S.C. §119 (e) of U.S. provisional application Ser. No. 61 / 114,216 filed on Nov. 13, 2008, herein incorporated by reference in its entirety.[0002]The present invention is related to a new class of polysiloxane copolymers with one or two terminal hydrophilic polymer chains. The present invention is also related to silicone hydrogel contact lenses prepared from a lens formulation containing a polysiloxane copolymer of the invention as an internal wetting agent.BACKGROUND OF THE INVENTION[0003]In recent years, soft silicone hydrogel contact lenses, for example, Focus NIGHT & DAY® and O2OPTIX™ (CIBA VISION), and PureVision® (Bausch & Lomb), Acuvue® Advance™ and Acuvue® Oasys™ become more and more popular because of their high oxygen permeability and comfort. “Soft” contact lenses conform closely to the shape of the eye, so oxygen cannot easily circumvent the lens. Soft contact lenses must allow oxygen from the surrounding air (i.e., ox...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08G77/442
CPCC08F293/00G02B1/043C08G77/442C08F299/08C08F283/12C08G77/04G02B1/04
Inventor PHELAN, JOHN CHRISTOPHERQIU, YONGXINGSCOTT, ROBERTWINTERTON, LYNN COOK
Owner ALCON INC
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